Abstract
The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C4-C14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into β-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1.
Original language | English |
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Pages (from-to) | 246-251 |
Number of pages | 6 |
Journal | Tetrahedron Asymmetry |
Volume | 22 |
Issue number | 2 |
DOIs | |
Publication status | Published - 2011 Jan 31 |
ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry